Processes for the production of sulfenamides by the reaction of primary or secondary amines with mercaptans such as 2-mercaptobenzothiazole in the presence of oxygen and a metal phthalocyanine catalyst, are described in U.S. Pat. No. 3,737,431. According to that description, the reaction can be carried out in a reaction medium which is an aqueous medium, a mixed aqueous-organic medium, or an organic medium. Most of the detailed examples are of processes in which the reaction medium contains a major amount of water relative to the amount of the primary or secondary amine, and the only wholly organic reaction media disclosed employ pyridine as the organic solvent.
U.K. Patent Specification No. 1,407,649 describes a process in which a 2-mercaptobenzothiazole is condensed with ammonia or a primary or secondary amine in the presence of oxygen using copper or a copper compound other than a copper phthalocyanine as a catalyst. The reaction medium may be aqueous, organic or aqueous organic, and when the reactant that is condensed with the 2-mercaptobenzothiazole is an amine, an excess of the amine can be used as the solvent for the reaction.